Methyl iodide → HCID 57791175, 화합물

HRID 1944716노트

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HRID 1944716 반응식
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Na+].[CH3:21]I>C1COCC1>[CH3:21][O:1][CH2:2][CH2:3][C@@H:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7016521tert-Butyl [(1R)-3-hydroxy-1-phenylpropyl]carbamate2회

생성물 1

HCID 57791175HCID 57791175, 화합물수율 29%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

(R)-tert-Butyl 3-hydroxy-1-phenylpropylcarbamate (Intermediate 60, 258 mg, 1.03 mmol) was dissolved in THF under nitrogen at 0° C. NaH was added and the reaction mixture was stirred at 0° C. for 10 min. MeI was added and the reaction mixture was stirred at room temperature for 30 min. then quenched with sat. aq. Na2SO4 and extracted with Et2O. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified via column chromatography using a biotage SP1 25+M column with a gradient 50% EtOAc in heptane calculated from TLC. Product fractions were combined and concentrated to give the title compound as a white solid (78 mg, 29%). LCMS=[M+H]=266

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 30 min.
  2. customthen quenched with sat. aq. Na2SO4
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via column chromatography
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4415569a1e7f415aaf5f599f37665c81
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394858B2

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